Airlines with flights from Chicago to Cancun
There are three airlines with scheduled flights between MDW and CUN. Southwest is the only airline with non-stop flights from Midway International Airport to Cancun International Airport and the flight time is 3 hours and 43 minutes.
There are three airlines with scheduled flights between MDW and CUN. Southwest is the only airline with non-stop flights from Midway International Airport to Cancun International Airport and the flight time is 3 hours and 43 minutes. Choose airline
Direct
Non-stop
3h 43min
Via Saint Louis
5h 10min
Via Atlanta
5h 15min
Via Nashville
5h 15min
Via Houston
5h 25min
Via Orlando
5h 25min
Via Austin
5h 50min
Via Baltimore
6h 5min
Via Atlanta
6h 46min
Starts 06/06
Via New Orleans
5h 15min
Starts 06/06
Via Kansas City
5h 45min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 3 hours and 43 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
14 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Direct
CUN
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN228
06:25
----
----
06:25
06:25
07:30
07:30
WN216
09:55
10:05
10:05
09:55
09:55
10:15
09:40
The timetable & schedule information was updated at 2026-04-21
Via Saint Louis with Southwest Airlines
-
Total flight time: 5h 10m - 8h 20m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
33 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via STL
CUN
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2900
WN1995
WN1995
07:50
08:20
08:20
07:50
07:50
06:30
08:05
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Delta Air Lines
-
Total flight time: 5h 15m - 9h 30m.
-
Sky Team Alliance
-
89 flights per week
MDW
Via ATL
CUN
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL1285
DL586
DL586
06:05
06:05
06:05
06:05
06:05
06:05
06:05
DL1063
DL1939
DL1939
11:05
11:05
11:05
11:05
11:05
10:55
11:05
DL2417
DL1939
DL1939
12:45
12:45
12:45
12:45
12:45
----
12:45
The timetable & schedule information was updated at 2026-04-21
Via Nashville with Southwest Airlines
-
Total flight time: 5h 15m - 9h 05m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
41 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via BNA
CUN
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN3855
WN386
WN386
----
----
----
----
----
----
06:10
WN1053
WN386
WN386
----
----
----
----
----
06:40
----
WN2959
WN386
WN386
07:15
08:40
08:40
07:15
07:15
----
----
WN1708
WN386
WN386
----
07:45
07:45
----
----
----
----
WN1337
WN386
WN386
----
----
----
----
----
----
07:55
WN1775
WN386
WN386
07:55
----
----
07:55
07:55
08:00
----
WN1257
WN386
WN386
09:00
----
----
09:00
09:00
----
----
WN2732
WN386
WN386
----
----
----
----
----
09:15
----
The timetable & schedule information was updated at 2026-04-21
Via Houston with Southwest Airlines
-
Total flight time: 5h 25m - 9h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
76 flights per week
-
Boeing 737-700 Passenger (Scimitar Winglets)Boeing 737MAX 8 Passenger
MDW
Via HOU
CUN
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2781
WN317
WN317
05:00
----
----
05:00
05:00
----
----
WN2781
WN315
WN315
----
----
----
----
----
05:05
----
WN4497
WN305
WN305
06:40
----
----
06:40
06:40
----
----
WN991
WN305
WN305
----
----
----
----
----
----
06:55
WN1772
WN305
WN305
----
----
----
----
----
07:05
----
WN4497
WN307
WN307
----
07:10
07:10
----
----
----
----
WN1180
WN317
WN317
----
----
----
----
----
07:40
----
WN2783
WN307
WN307
10:10
10:15
10:15
10:10
10:10
----
----
WN1301
WN317
WN317
----
----
----
----
----
10:35
----
WN1674
WN317
WN317
----
----
----
----
----
----
10:40
The timetable & schedule information was updated at 2026-04-21
Via Atlanta with Frontier